JPH0826005B2 - Pyrazole derivatives and insecticides and acaricides containing the same as active ingredients - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a novel pyrazole derivative and insecticides and acaricides containing the same as an active ingredient.

[Conventional technology]

Examples of compounds having a structure similar to the compound of the present invention include those having bactericidal activity. Pest.Bio.Phy., 25 , 163
(1986), JP-A-52-87168 and JP-A-60-349.
Japanese Patent Application Laid-Open No. 57-10 has a herbicidal activity.
Japanese Patent No. 6665 and those having pharmaceutical activity are disclosed in JP-A-47-
6269, JP-A-48-56671, JP-A-52-83840
JP-B, JP-B-55-44751, JP-A-56-73071, JP-A-59-95272 and J. Pharm. Sci., 74 , 101.
3 (1985), but there is no report on insecticidal and acaricidal activity. Further, the above-mentioned publications and documents do not describe an aralkyl group as a substituent of an amino moiety at all.

On the other hand, in Farmaco, Ed.Sci., 22 , 629 (1967), N-benzyl-3-methyl-5-pyrazolecarboxamide and 3-methyl-5-pyrazolecarboxylic acid benzyl ester are also described in Rev. Roum. Chim., 23 , 1581 (1978), N-benzyl-1- (2,4-dinitrophenyl)-
3-biphenyl-5-pyrazolecarboxamide, and in JP-A-50-58056, N- (4-hydroxybenzyl) -1,3-dimethyl-5-pyrazolecarboxamide and N- (4-hydroxycarbonylmethoxy). Benzyl) -1,3-dimethyl-5-pyrazolecarboxamide is described, but there is no report on the presence or absence of insecticidal and acaricidal activity of the compound.

Although the prior art has been described in detail above, no compound has been reported in which the acid moiety is a bicyclic pyrazole and the amine and (thio) alcohol moieties are aralkyl.

[Problems to be solved by the invention]

In recent years, the use of insecticides for many years has caused resistance to harmful insects, making it difficult to control them with conventional insecticides. For example, resistance pests are widely generated against organic insecticides and carbamate agents, which are typical insecticides, and it is difficult to control them. In addition, the development of resistance to synthetic pyrethroid insecticides, which has been attracting attention in recent years, has been reported. On the other hand, some of the organophosphorus agents or carbamate agents are highly toxic, and some of them disturb the ecosystem due to persistence, which is a very alarming situation. Therefore, development of a novel insecticide having excellent control effect against harmful insects resistant to conventional insecticides and having low toxicity and low residue is expected.

[Means for solving problems]

As a result of intensive studies to cope with such a situation, the present inventors have found a novel pyrazole derivative having excellent insecticidal and acaricidal activity.

That is, the gist of the present invention is the following general formula (I) [In the above formula, R and R ¹ are each independently a hydrogen atom or
C _{1 to} C _{4 is} an alkyl group, R ² is bonded to one of the nitrogen atoms of the pyrazole ring, and is a hydrogen atom, a C _{1 to} C ₄ alkyl group, a phenyl group or a benzyl group, X Represents an oxygen atom, a sulfur atom, NR ⁷ or NHO, Y represents an oxygen atom or a sulfur atom, R ³ and R ⁴ are each independently a hydrogen atom, a C ₁ -C ₄ alkyl group or a phenyl group. shown, R ⁷ represents a hydrogen atom or an alkyl group C ₁ ~C _4, R ⁵ and R ⁶ are each independently a hydrogen atom, a halogen atom, an alkyl group of _{C 1 ~C 6, C 3 ~C} 6 a cycloalkyl group, an alkoxy group of _{C 1 ~C 4, C 1 ~C} 4 of halogenoalkoxy group C ₁ -C ₄ hydroxy alkoxy group, alkoxyalkoxy group of C ₂ -C _7, a nitro group, trifluoromethyl group, a phenyl group, a phenoxy group, a benzyloxy group, an amino group, alkylamino C ₁ -C ₄ , Dialkylamino group C ₂ -C _8, cyano group, carboxyl group, C ₂ -C ₅ alkoxycarbonyl group, C ₄ -C ₇ cycloalkoxy carbonyl group, alkoxyalkoxy group of C ₃ -C _9, C alkylaminocarbonyl group ₂ -C _7, dialkylaminocarbonyl group of C ₃ -C _11, piperidinocarbonyl group, morpholinocarbonyl group, trimethylsilyl group, an alkylthio group of C ₁ -C _4, alkyl C ₁ -C ₄ A sulfinyl group or a C ₁ -C ₄ alkylsulfonyl group is shown, m is 1 or 2, and n is 0 or 1. ] It exists in the pyrazole derivative represented by these, and the insecticide and acaricide containing this as an active ingredient.

 Hereinafter, the present invention will be described in detail.

In the general formula (I), R and R ¹ are each independently a hydrogen atom; methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group. And C _{1 to} C ₄ straight chain or branched chain alkyl groups. R ² is a hydrogen atom; methyl group, ethyl group, n
- propyl group, an isopropyl group, n- butyl group, isobutyl group, sec- butyl group, a C ₁ -C ₄ in a t- butyl group and the like straight or branched chain alkyl group; a phenyl group; or a pyrazole ring shown benzyl Is bound to one of the nitrogen atoms. Among these substituents, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group,
C _{1 to} C such as isobutyl group, sec-butyl group, t-butyl group
Preferably a linear or branched alkyl group of _4, the bonding position is preferably a nitrogen atom at the 2-position of the pyrazole ring. X represents an oxygen atom, a sulfur atom, NR ⁷ (R ⁷ represents a hydrogen atom or a C _{1 to} C ₄ alkyl group) or NHO, and preferably NH. Y represents an oxygen atom or a sulfur atom, and preferably an oxygen atom. R ³ and R ⁴ are each independently a hydrogen atom;
Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t
A C ₁ -C ₄ linear or branched alkyl group such as a butyl group;
Alternatively, it represents a phenyl group, preferably a hydrogen atom. R ⁷
Is a hydrogen atom; a C ₁ -C ₄ linear or branched alkyl group such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a t-butyl group. And is preferably a hydrogen atom. R ⁵ and
R ⁶ is independently a hydrogen atom; a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom; a methyl group, an ethyl group, an n-propyl group, an isopropyl group, n-
Butyl group, isobutyl group, sec-butyl group, t-butyl group, n-amyl group, isoamyl group, t-pentyl group, n
-Hexyl group, 1-ethyl-1-methylpropyl group, etc.
C _{1 to} C ₆ linear or branched alkyl group; C _{3 to} C ₆ cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group; methoxy group, ethoxy group, n-propoxy group, iso Propoxy group, n-butoxy group, isobutoxy group, sec-butoxy group, t-butoxy group and other C _{1 to} C ₄ linear or branched alkoxy groups; monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group,
Chloromethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 3-chloropropoxy group, 4-chlorobutoxy group, 4-bromobutoxy group, 1,1-dimethyl-2-
A C ₁ -C ₄ halogenoalkoxy group such as a chloroethoxy group;
Hydroxymethoxy group, 2-hydroxyethoxy group, 3
- hydroxypropoxy group, 4-hydroxy-butoxy hydroxyalkoxy group C ₁ -C _4, such as a group; methoxymethoxy group, ethoxymethoxy group, a methoxyethoxy group, methoxy sheet propoxy group, methoxy butoxy group, ethoxyethoxy group, propoxyethoxy group , butoxyethoxy group, C ₂ -C ₇ alkoxyalkoxy group such as butoxy propoxy group; a nitro group; trifluoromethyl group; a phenyl group; a phenoxy group; a benzyloxy group; an amino group; methylamino group, an ethylamino radical, n -Propylamino group,
Isopropylamino group, n- butylamino group, isobutylamino group, sec- butyl group, C ₁ -C ₄ straight or branched chain alkylamino group such as t- butylamino group; a dimethylamino group, diethylamino group, di -N-propylamino group, diisopropylamino group, di-n-butylamino group, diisobutylamino group, N-ethylmethylamino group, N-methylpropylamino group, Nn-butylethylamino group, N-isobutylethyl group C _2- such as amino group
C ₈ di (linear or branched) alkylamino group; cyano group; carboxyl group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group , Sec-butoxycarbonyl group,
linear or branched alkoxycarbonyl group having C ₂ -C _5, such as a t- butoxycarbonyl group; cycloalkyl propoxycarbonyl group, a cycloalkyl-butoxycarbonyl group, cyclopentyloxy group, cycloalkoxy of C ₄ -C ₇ and cyclohexyl oxycarbonyl group Carbonyl group; methoxymethoxycarbonyl group, methoxyethoxycarbonyl group,
Methoxypropoxycarbonyl group, methoxybutoxycarbonyl group, ethoxyethoxycarbonyl group, n-propoxyethoxycarbonyl group, isopropoxyethoxycarbonyl group, n-, iso-, sec-, t-butoxyethoxycarbonyl group, hexyloxyethoxycarbonyl group, etc. C ₃ -C ₉ alkoxycarbonyl alkoxycarbonyl group; methylamino group, ethylamino carbonyl radical, n
- propylamino group, isopropylamino group, n-, iso -, sec-, t-butylamino group, pentyl aminocarbonyl group, alkylaminocarbonyl group C ₂ -C ₇ hexyl amino group; dimethyl C ₃ such as aminocarbonyl group, diethylaminocarbonyl group, dipropylaminocarbonyl group, dibutylaminocarbonyl group, dipentylaminocarbonyl group, methylethylaminocarbonyl group, methylpropylaminocarbonyl group, ethylbutylaminocarbonyl group
To C ₁₁ dialkylaminocarbonyl group; piperidinocarbonyl group; morpholinocarbonyl group; trimethylsilyl group; methylthio group, ethylthio group, n-propylthio group, isopropylthio group, n-butylthio group, isobutylthio group, sec-butylthio group , C such as t-butylthio group
₁ -C ₄ straight or branched chain alkylthio group; methylsulfinyl group, ethylsulfinyl group, n- propyl sulfinyl group, isopropyl sulfinyl group, n- butyl sulfinyl group, isobutyl sulfinyl group, sec- butyl sulfinyl group, t- butyl C ₁ such as sulfinyl group
To a C ₄ linear or branched alkylsulfinyl group; or a methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, t- It represents a linear or branched alkylsulfonyl group having C ₁ -C _4, such as a butylsulfonyl group, preferably
R ⁵ is a hydrogen atom. m is 1 or 2, n is 0 or 1, and preferably m is 1 and n is 0.

The compound of the present invention represented by the general formula (I) can be produced according to the following reaction scheme.

[In the above reaction formula, R, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , X,
Y, m and n are as defined in the general formula (I), Z is a chlorine atom, a bromine atom, a hydroxyl group, a methoxy group,
An ethoxy group or a propoxy group is shown. In the above general formula (II), when Z represents a chlorine atom or a bromine atom, an aromatic hydrocarbon such as benzene, toluene or xylene; a ketone such as acetone, methyl ethyl ketone or methyl isobutyl ketone; chloroform or methylene chloride. Halogenated hydrocarbons such as; water; esters such as methyl acetate or ethyl acetate; tetrahydrofuran,
In a polar solvent such as acetonitrile, dioxane, N, N-dimethylformamide, N-methylpyrrolidone or dimethylsulfoxide, a compound represented by the general formula (III) at 0 to 30 ° C., preferably 0 to 5 ° C., in the presence of a base, By reacting, the compound of the above general formula (I) can be obtained. Examples of the base include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine and the like.

Further, in the general formula (II), when Z represents a hydroxyl group, a methoxy group, an ethoxy group or a propoxy group, no solvent or a high boiling solvent such as N, N-dimethylformamide, N-methylpyrrolidone or dimethylsulfoxide is used. , 150
-250 ° C, preferably 200-250 ° C, by reacting the compound represented by the general formula (III) with the above general formula (I)
Can be obtained.

The compound represented by the general formula (II) is, for example, An
It can be produced according to the method described in n. Chem., 536 , 97 (1938).

[Action]

The compound represented by the general formula (I) is an insect such as Coleoptera, Lepidoptera, Hemiptera, Orthoptera, Diptera, etc., and eggs of the order Acarina,
It has a remarkable controlling activity on larvae, but is not limited to these.

1 Hemiptera; planthoppers such as sedge brown planthoppers, brown planthoppers, and leafhoppers, leafhoppers such as leafhoppers and leafhoppers, aphids such as green peach aphids 2 Lepidoptera: Lotus japonicus, Nikameichu 4 and 3 pods, etc. Eyes; house fly, Aedes aegypti, Culex pipiens, etc. 5 Acarida: Nami mites, Nicaria mites, mandarin mites, etc. When the compound of the present invention represented by the general formula (I) is used as an insecticide or acaricide, it may be used alone. However, usually, an emulsion using an auxiliary agent as with conventional pesticides,
It is formulated in the form of powder, wettable powder, liquid, etc. and used as it is or after dilution. As the auxiliary agent, the usual ones used in the formulation of insecticides are used. For example, solid carriers such as talc, kaolin, diatomaceous earth, clay, starch, water, hydrocarbons such as cyclohexane, benzene, xylene, toluene, halogenated hydrocarbons such as chlorobenzene, ethers, amides such as dimethylformamide, Examples thereof include solvents such as ketones, alcohols, nitriles such as acetonitrile, and other known surfactants such as emulsifiers and dispersants.

If desired, they can be mixed or used in combination with other insecticides, acaricides, fungicides, insect growth regulators, plant growth regulators and the like.

The concentration of the active ingredient in the formulated insecticide and acaricide is not particularly limited, but is usually 0.5 to 20% by weight, preferably 1 to 10% by weight in a powder, and 1 to 90% by weight in a wettable powder. Is 10 to 80% by weight, the emulsion is 1 to 90% by weight, preferably 10
Contains -40% by weight of active ingredient.

When the compound represented by the general formula (I) is used as an insecticide, the active ingredient is usually 5 to 1000 ppm, preferably 1
Used in the concentration range of 0 to 500 ppm.

〔Example〕

Next, the present invention will be described more specifically with reference to Production Examples, Formulation Examples, and Test Examples of the compound of the present invention, but the present invention is not limited to the following examples unless it exceeds the gist.

Example 1 N- (4-t-butylbenzyl) -2-methyl-4,5,6,
Preparation of 7-Tetrahydro-3- (2H) -indazolecarboxamide 2-Methyl-4,5,6,7-tetrahydro-3- (2H)-
1 g of 1.80 g of indazolecarboxylic acid and 11.7 g of thionyl chloride
Heated to reflux for hours. After thionyl chloride was distilled off under reduced pressure, the residue was dissolved in 20 ml of toluene. This was mixed with 4-t-butylbenzylamine (1.96 g) and triethylamine (1.21 g) in toluene 25
It was added dropwise to the ml solution at 0-5 ° C. After dropping, the mixture was stirred for 2 hours, poured into ice water, and extracted with toluene. The toluene layer was washed with an aqueous sodium carbonate solution, water, and saturated saline. After drying over anhydrous sodium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain Compound No. 182.88 g shown in Table-1.

The NMR and IR of this compound are as follows. _{^{1 HNMR (CDC1 3) δppm;}} 1.3 (S, 9H), 1.7 (m, 4H), 2.6
(M, 4H), 4.05 (S, 3H), 4.5 (d, 2H), 5.8 (b, 1
H), 7.3 (m, 4H) IR (KBr) cm ^-1 ; 3362, 2932,1636,1540,1145,1293,970,5
90 Example 2 Preparation of N- (4-t-butylbenzyl) -2-methylcyclopenta [1,2-C] -3-pyrazolecarboxamide 2-Methyl-cyclopenta [1,2-C] -3-pyrazole Carboxylic acid ethyl ester (1.94 g) and 4-tert-butylbenzylamine (2.45 g) were heated and stirred at 200 ° C. for 4 hours. After cooling to room temperature, it was purified by silica gel column chromatography to obtain 2.15 g of compound No. 6 shown in Table-1.

The NMR and IR of this compound are as follows. _{^{1 HNMR (CC1 4) δppm;}} 1.35 (S, 9H), 2.3~2.8 (m, 6
H), 4.1 (S, 3H), 4.5 (d, 2H), 5.8 (b, 1H), 7.25
(M, 4H) IR (KBr) cm ^-1 ; 3310,2960,1640,1560,1540,1370,1320,5
80 Example 3 Preparation of N- (4-n-butylbenzyl) -2,4,6-trimethylcyclopenta [1,2-C] -3-pyrazolecarboxamide 2,4,6-trimethyl-cyclopenta [1, 2-C] -3-
1.94 g of pyrazolecarboxylic acid and 11.7 g of thionyl chloride were heated under reflux for 1 hour. After thionyl chloride was distilled off under reduced pressure, the residue was dissolved in 20 ml of ethyl acetate. This was added dropwise to a solution of 4-n-butylbenzylamine (1.96 g) and triethylamine (1.21 g) in ethyl acetate (25 ml) at 0 to 5 ° C. After dropping, the mixture was stirred for 2 hours, poured into ice water, and extracted with ethyl acetate. The ethyl acetate phase was washed with an aqueous sodium carbonate solution, water, and saturated saline. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the compound shown in Table 1 was first added.
I got No.68. Then, Compound No. 69 described in Table 1 was obtained. N
o.68 and No.69 are diastereomers.

 The NMR, IR and MASS of this compound are as follows.

No.68 spectrum ¹ HNMR (CDC1 ₃ ) δppm; 0.9 (m, 3H), 1.05 (d, 3H), 1.2
5 (d, 3H), 1.0 to 1.8 (m, 4H), 2.15 (m, 2H), 2.55
(T, 2H), 3.1 (m, 2H), 4.1 (S, 3H), 4.5 (d, 2H),
5.95 (d, 1H), 7.25 (m, 4H) IR (KBr) cm ^-1 ; 3280,2950,2860,1635,1550,1530,1450,1
370,1275,980,810,530 No.69 spectrum ¹ HNMR (CDC1 ₃ ) δppm; 0.9 (m, 3H), 1.2 (d, 3H), 1.3
(D, 3H), 1.0 to 1.8 (m, 4H), 2.6 to 3.3 (m, 6H), 4.15
(S, 3H), 4.55 (d, 2H), 6.0 (b, 1H), 7.25 (m, 4H) IR (KBr) cm ^-1 ; 3290,2950,1640,1550,1520,1300,980,80
0,520 Example 4 Table-1 and Table-2 according to the method of Example 1, 2 or 3.
The compound described is obtained.

Next, formulation examples of the compound of the present invention will be shown. In the following, "parts" and "%" mean "parts by weight" and "% by weight", respectively.

Formulation Example 1: Wettable powder 20 parts of the compound of the present invention shown in Tables 1 and 2, Carplex # 80 (Shionogi Pharmaceutical Co., Ltd., trade name) 20 parts, N, N Kaolin clay (Tsuchiya Kaolin Co., trade name ) 55 parts and 5 parts of a higher alcohol sulfate ester type surfactant Solpol 8070 (trade name of Toho Kagaku Co., Ltd.) were mixed and uniformly pulverized to obtain a wettable powder containing 40% of the active ingredient.

Formulation Example 2: Dust formulation 2 parts of the compound of the present invention shown in Tables 1 and 2, 93 parts of clay (manufactured by Nippon Talc Co., Ltd.) and 5 parts of white carbon were uniformly mixed and pulverized to produce a 2% powder formulation.

Formulation Example 3: Emulsion 20 parts of the compound of the present invention shown in Table 1 and Table 2 was mixed with xylene.
It is dissolved in a mixed solvent consisting of 35 parts and 30 parts of dimethylformamide, and 15 parts of polyoxyethylene-based surfactant Solpol 3005X (Toho Chemical Co., Ltd., trade name) is added thereto,
An emulsion containing 20% of the active ingredient was obtained.

Formulation Example 4: Flowable agent 30 parts of the compounds of the present invention shown in Tables 1 and 2, 8 parts of ethylene glycol premixed, Solpol AC30
5 parts of 32 (trade name of Toho Kagaku Co., Ltd.) and 0.1 parts of xanthan gum were thoroughly mixed and dispersed in 56.9 parts of water. Next, this slurry-like mixture was wet-milled with Dynomill (Shinmaru Enterprises Co., Ltd.) to obtain a stable flowable agent containing 30% of the active ingredient.

Test Example 1 Effect on adults of Nite mite A leaf disc (diameter 2 cm) of kidney bean leaves is inoculated with 10 female adults of Nite mite. 5 ml of a liquid obtained by diluting the compound of the present invention prepared according to the method of Preparation Example 1 with water to a predetermined concentration was applied thereto using a rotary spraying tower (manufactured by Mizuho Rika).

(1 concentration, 2 repetitions) 24 hours after the treatment, the life and death of adults were investigated and the miticidal rate (%) was calculated. The results are shown in Table-3.

Test Example 2 Effect on the eggs of Nite mites The leaf discs (2 cm in diameter) of kidney bean leaves are released with 5 female adults of Nite mites. After release, the leaves were laid on a leaf disk for 20 hours, and then female adults were removed. To this, 5 ml of a liquid prepared by diluting the compound of the present invention prepared according to the method of Preparation Example 1 to a predetermined concentration with water was sprayed using a rotary spraying tower (manufactured by Mizuho Rika). (1 concentration, 2 repetitions) Five days after the treatment, the number of unhatched eggs and the number of hatched adults were examined to determine the egg killing rate (%). The results are shown in Table-3.

Test Example 3 Effect on the larva of the brown planthopper The seedlings of rice planted in a glass cylinder (diameter: 3 cm, length: 17 cm) are set, and five fourth-instar larvae of the plant plant are released. 0.5 ml of a liquid obtained by diluting the compound of the present invention prepared according to the method of Preparation Example 3 with water was sprayed onto this using a spray tower (Mizho Rika). (1 concentration, 4 repetitions) Five days after the treatment, the larvae were examined for life and death, and the insecticidal rate (%) was determined. The results are shown in Table-4.

Test Example 4 Effect on diamondback moth larvae Cut leaves of cabbage (5 × 5 cm) were immersed for 1 minute in a liquid obtained by diluting the compound of the present invention prepared according to the method of Preparation Example 1 with water. Air-dried after immersion, plastic cup (diameter 7 cm)
5 third-instar larvae of Plutella xylostella were released (1 concentration, 2 repetitions).

Four days after the release, the larvae were examined for life and death, and the insecticidal rate (%) was calculated. The results are shown in Table-5.

[Effect of the Invention] As is clear from the above test examples, the pyrazole derivative of the present invention is useful as an insecticide and acaricide.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yoji Takahashi 1000 Kamoshida-cho, Midori-ku, Yokohama, Kanagawa Sanryo Kasei Co., Ltd. (72) Inventor Toshiki Fukuchi, 1000, Kamoshida-cho, Midori-ku, Yokohama, Kanagawa Ryokasei Co., Ltd.

Claims (4)

[Claims] 1. A pyrazole derivative represented by the following general formula (I). [In the above formula, R and R ¹ are each independently a hydrogen atom or
C _{1 to} C _{4 represents} an alkyl group, R ² represents a hydrogen atom, a C _{1 to} C ₄ alkyl group, a phenyl group or a benzyl group bonded to either nitrogen atom of the pyrazole ring, and X represents oxygen. Atom, sulfur atom, NR ⁷ or NHO, Y represents an oxygen atom or a sulfur atom, R ³ and R ⁴ each independently represent a hydrogen atom, a C ₁ -C ₄ alkyl group or a phenyl group, R ⁷ represents a hydrogen atom or a C _{1 to} C ₄ alkyl group, R ⁵ and R ⁶ are each independently a hydrogen atom, a halogen atom, a C _{1 to} C ₆ alkyl group, a C _{3 to} C ₆ cyclo group. alkyl group, C ₁ -C ₄ alkoxy groups, C ₁ -C ₄ halogenoalkyl alkoxy group, hydroxyalkoxy group of C ₁ -C _4, an alkoxyalkoxy group of C ₂ -C _7,
Nitro group, trifluoromethyl group, phenyl group, phenoxy group, benzyloxy group, amino group, C _{1 to} C ₄ alkylamino group, C _{2 to} C ₈ dialkylamino group, cyano group,
Carboxyl group, an alkoxycarbonyl group having C ₂ ~C _5, C ₄
To C ₇ cycloalkoxycarbonyl group, C _{3 to} C ₉ alkoxyalkoxycarbonyl group, C _{2 to} C ₇ alkylaminocarbonyl group, C _{3 to} C ₁₁ dialkylaminocarbonyl group, piperidinocarbonyl group, morpholinocarbonyl group Group, trimethylsilyl group, C ₁ -C ₄ alkylthio group, C ₁
To C ₄ alkylsulfinyl group or C _{1 to} C ₄ alkylsulfonyl group, m is 1 or 2, and n is 0 or 1. ] 2. R ² is a C ₁ -C ₄ alkyl group, Y is an oxygen atom, X is NR ⁷ , R ³ , R ⁴ , R ⁵ and R ⁷ are all hydrogen atoms, and n Is 0, wherein
The pyrazole derivative described in 1. 3. The pyrazole derivative according to claim 2, wherein R ² is bonded to the nitrogen atom at the 2-position of the pyrazole ring and m is 1. 4. An insecticide and acaricide containing the pyrazoles according to claim 1 as an active ingredient.